Cheap flights from Toronto to Chicago from C$ 116
This is the cheapest one-way flight price found by a momondo user in the last 72 hours by searching for a flight from Toronto to Chicago departing on 1/9. Fares may change, and may not be available for all flights or travel dates. Click the price to refresh the search for this deal.
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American Airlines flights from Toronto to Chicago
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Air Canada flights from Toronto to Chicago
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How to get the cheapest flight ticket from Toronto to Chicago
Look no further. We've gone through all the searches for this route on momondo so you have the important information and insights to find the cheapest flight ticket for your trip
What is the typical price of a round-trip flight between Toronto and Chicago?
What is the cheapest month to fly to Chicago?
The month of April is another great option to travel to Chicago, with average flight prices from Toronto averaging around C$ 350.
What is the cheapest day to depart on your flight to Chicago?
The cheapest day to depart on your flight to Chicago is on a Friday when prices can be found for as low as C$ 737. This is often the case because there is less demand to fly during this day of the week. If your travel schedule is flexible, try to avoid departing on a Tuesday because tickets tend to average around C$ 1,375. These prices are subject to change though, so be sure to set up a Price Alert for flights to Chicago.
What is the cheapest time of day to depart on your flight to Chicago?
In the evening is the cheapest time of day to fly from Toronto to Chicago when you can find flight prices for as low as C$ 548. Flying to Chicago in the evening is an ideal time because this is during off-peak travel hours. In the afternoon is when there is more demand to fly to Chicago, so prices are often more expensive at around C$ 1,554 per ticket.
What is the cheapest Toronto to Chicago flight route?
Fly from Toronto Island to Chicago Midway for the best Toronto - Chicago flight prices
How far in advance should I book a flight to Chicago?
You are more likely to see cheaper flights to Chicago from Toronto when booking 16 weeks ahead of your departure date. In general, you can expect to find flights to Chicago for around C$ 418 when searching 16 weeks out.However, flight prices might be lower outside of this timeframe. For example, people recently found flights to Chicago from Toronto for as low as C$ 363 on momondo.
What cabin class options are available on Toronto to Chicago flights?
There are 4 cabin classes available to choose from on Toronto to Chicago flights. Cabin price and availability will vary by airline so perform a search above to find the right deals for you.
What is the cheapest airline that flies from Toronto to Chicago?
Porter Airlines, Air Canada, and Air Transat are the most popular carriers operating from Toronto to Chicago
Which airlines fly to Chicago?
Air Canada, United Airlines and Porter Airlines are the top three most popular airlines that fly to Chicago from Toronto according to our data. Air Canada is the first choice among our users, with 68% of people opting to fly with this airline when travelling to Chicago. Keep in mind that there are 5 different airlines that fly to Chicago on a routine basis, so you have a few additional options to choose from.
How many flights depart from Toronto to Chicago on average per day?
44 flights are operational daily from Toronto to Chicago as of April 2025. The most popular departure time for this route is 3:00p.m., with 46% of flights per day taking off in the afternoon.
How many flights depart from Toronto to Chicago on average per week?
311 flights are operational weekly from Toronto to Chicago as of April 2025. The most popular departure day for this route is Wed, with 20% of flights per week taking off on this day.
When to book flights from Toronto to Chicago
Cheap Toronto to Chicago (YTO to CHI) flight deals and tips
Find info about flight duration, direct flights, and airports for your flight from Toronto to Chicago
How far is Toronto to Chicago by plane?
Chicago is 700.6 km away from Toronto. Flights usually cover this in 1h 49m, depending on flying conditions and air traffic around both airports.
When did momondo last update prices for flights from Toronto to Chicago?
Prices for flights from Toronto to Chicago are updated daily.
How many operators does momondo search for flights from Toronto to Chicago?
There are 5 operators available for flights from Toronto to Chicago as of April 2025.
How old do you have to be to fly from Toronto to Chicago?
Although the minimum age for a child to fly alone is five, airlines that offer an unaccompanied minor (UMNR) service may have their own age limits, which could be impacted by factors such as flight length, timing, and layovers. It is recommended that you verify with the airline you are booking with for travel from Toronto to Chicago.
What documentation or ID do you need to fly to Chicago?
The required travel and health documents for your Chicago trip may vary depending on your itinerary and personal circumstances. As a general rule, you should carry multiple documents, including a national ID card or driver's license and a passport valid for six months after your intended arrival at Chicago. We recommend that you seek guidance from your airline or a reliable third party such as IATA.
What is the most popular plane model from Toronto to Chicago?
Based on momondo bookings for this flight route, the most popular plane model on flight routes from Toronto to Chicago is De Havilland (Bombardier) DHC-8-400 Dash 8Q (17.45% of total bookings). The next most popular plane models are Embraer 175 (Enhanced Winglets) (13.30%), Airbus A220-300 (8.84%), and Boeing 737 MAX 8 (7.94%).
What is the most popular airline from Toronto to Chicago?
Based on momondo bookings for flights between Toronto and Chicago, the leading airline is Porter Airlines, making up 63% of the total bookings. Other popular airlines include Air Canada with 25%, United Airlines with 5%, and Air Transat with 4%.
Best airlines flying from Toronto to Chicago
Compare and see reviews for airlines that fly from Toronto to Chicago with momondo
| Airline | Rating | Free Cancellation | Price | ||
|---|---|---|---|---|---|
| PriceFrom C$ 260 | Free Cancellation | Rating 8.0 285 reviews | |||
| PriceFrom C$ 300 | Free Cancellation | Rating 7.2 10,000 reviews | |||
| PriceFrom C$ 301 | Free Cancellation | Rating 7.0 9,245 reviews | |||
| PriceFrom C$ 329 | Free Cancellation | Rating 7.4 8,696 reviews | |||
| PriceFrom C$ 428 | Free Cancellation | Rating 7.2 2,826 reviews |
Porter Airlines Flights From Toronto to Chicago
Across 6 Porter Airlines flights from Toronto to Chicago this week, the average price was C$ 263, with the best Porter Airlines deals starting from C$ 188 round-trip. 285 users have rated Porter Airlines on momondo, with an average score of 8.0/10.
United Airlines Flights From Toronto to Chicago
United Airlines is also a popular choice for this route. United Airlines flight deals for Toronto to Chicago start from as low as C$ 238 round-trip, depending on your selected dates, with average United Airlines deals seen on momondo around C$ 327. United Airlines operates 39 flights to Chicago from Toronto in an average week. Users have rated it 7.4/10 across 8,696 reviews.
Travelling to a place near Chicago?
Book flights to Chicago if you plan to visit one of these locationsWhy use momondo?
Why should I use momondo to find a flight deal from Toronto to Chicago?
To find the flight that best suits your needs, momondo gathers a range of flights from a large pool of different airlines and agents; you can then use our insights and filters to find and book the right flight to Chicago from Toronto.
Can I find flights from Toronto to Chicago with flexible booking policies on momondo?
Yes. All flights to Chicago from Toronto on momondo can be compared and filtered by various policies on offer, including flexible booking.
How can momondo help me find flights from Toronto to Chicago?
Once you have performed a search in the form on the page, momondo provides useful filters and insights. We can show you the cheapest days and times to fly as well as help filter your options to help you make an informed choice when booking flights to Chicago from Toronto.
I’m not ready to book a flight from Toronto to Chicago right now. Can momondo alert me if prices change?
Of course. momondo tracks the price of Toronto to Chicago flights. All you need is a valid email address and we will do the rest; it is that quick and easy.